Roommate Swears He Needs A Bigger Condom [F24, M23][Roommates][Proving His Size][Huge Dick][Broken Condom][Female Orgasm][May 2026 Contest][Image 1]

This story is inspired by Image 1.

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“GODDAMMIT! WHERE IS IT?”

I exhale frustratedly and look up from my book as I listen to my roommate thrash around his room in search of something. As he continues loudly tossing things about, I take a deep breath and try to block it out so I can return to my studies.

“FUCK! IT’S NOT HERE!” he screams loudly, breaking my focus.

I let out an exasperated grunt, slam my book shut and toss it onto my bed, before storming out across the hall. I forcefully push open his door and exclaim “Can you please keep it down? I’m trying to read!”

I spot him on his hands and knees searching through a big cardboard box. All of his things are strewn about the room messily. He looks up to me frantically. “Sorry. I just really have to find this tonight and it’s just not here,” he says as he stands up and hops his way to the other side of the room and begins looking through more containers.

“Well. Can you tell me what it is you’re looking for? So I can help you find it and you can stop being so fucking loud.”

“Be my guest,” he responds, gesturing to the room around him. “I’m looking for a black box of Trojans,” he states while continuing to rummage around.

I cross my arms. “Trojans?”

“Yep.”

“Like the condoms?”

“Correct.”

“That’s what all this is about?”

“Yeah. I have a date tonight. And I’m not about to be illprepared.”

I throw my hands up in the air. “Jesus Christ!” I turn around and storm out of the room and back over to mine. I quickly make my way over to my nightstand. I pull open the drawer and pull out a condom with a light blue wrapper, before returning back to his room. “If you needed a condom you could have just asked,” I say as I toss it over to him.

It hits him on his shoulder and drops to the floor. He turns and picks it up and looks at it for a moment, before looking up at me. “Not gonna work.” He flicks it back to me.

“What do you mean ‘not gonna work’?” I ask annoyedly.

“Too small,” he says as he opens a new box to begin digging through.

I begin to laugh. “Yeah okay. Too small. Sure,” I say, fully not believing him.

“It is! It won’t work.”

“Whatever dude,” I seat myself on his bed. “If your pride is so great, that you’re going to turn down a perfectly good condom and risk not getting laid, then that’s on you.”

“I’m telling you it won’t work. I’ve tried. I have to order specially fitted ones and I know that I have another box around here somewhere.”

“You’re so dumb. Don’t you know that condom companies only sell those so they can appease the fragile egos of men who need to feel more ‘like a man’ or whatever.”

He stops searching for a moment and takes a deep breath. I can tell he’s starting to get annoyed. “That may be true for some men. But this is the only thing that works for me. So if you aren’t going to help, can you please leave?”

“Do you really believe that though? I’ve seen someone stick their entire arm inside of a condom without it breaking. And you sure as shit aren’t that big.”

“It’s closer than you’d think,” he mutters under his breath almost inaudibly.

“What was that?” I prod.

“Nothing. It’s not a fair comparison. If that person also wasn’t having to worry about bloodflow, and the ability to feel pleasure, while also dealing with sliding in and out of a vagina, then you shouldn’t just accept that there’s no use for larger condoms.”

“I’m just saying that nobody that I’ve ever slept with has complained about these,” I say holding up the condom.

“Well you haven’t slept with me.”

“Ooh. Big boy!” I taunt. “I can hardly believe it.”

He slams down the various things that he has in his hands back into the box. “If I show you, will that shut you up?”

I gasp lightly at the sudden proposal but don’t want to give away any upperhand that I have. “Well, you’d have to be right. Which I highly doubt.”

He quickly stands up off of his knees and makes his way over to the side of the bed that I am sat. He stands before me and grabs the band of his sweatpants. “You really don’t believe me? Well here, take a look.”

He swiftly pulls his pants down below his knees. My eyes immediately land on his penis hanging between his legs. I gulp suddenly upon seeing it. His cock is long and thick. I immediately recognize that it is bigger than most of the men that I’ve slept with before. I feel my heart start to race and find myself wanting to touch it, but force myself to hold my composure.

Seconds of silence pass as I continue to gaze upon it. “Well?” he asks, awaiting some sort of commentary from me.

I gulp to clear my throat before replying. “Well…it’s a decent size. But you could still fit that in a condom.” I say, unwilling to give him the satisfaction of being right.

“That’s because it’s not hard,” he growls back.

He moves his hand to his dick and wraps his fingers around it. He begins to slowly stroke up and down his shaft to give himself an erection. With each passing moment I can tell that he is getting larger and larger.

I eventually speak up. “We shouldn’t do this. We-we’re roommates. This is weird.”

“You can go. But this is my room, so I’m going to do as I please,” he says as he continues massaging his still growing cock.

Despite knowing that I have the option to leave, I find myself paralyzed in awe of watching him and can’t muster the ability to leave. I can feel my jaw drop as I continue to examine. The blood rushes into his cock filling it to its maximum potential. Before long I am left staring as his hands work along a long, girthy dick jutting from his body.

My breath hastens as I admire the specimen before me. As his right hand continues to pump the impressive length of his meat, his left hand raises before me. He opens his palm and reveals the wrapped condom I had thrown to him before.

“See if it fits,” he says, almost as a dare.

I extend my hand and take the condom. I look from the square packaging to the enormous cock standing before me. I use my other hand to tear the blue wrapper, being careful to not damage the actual product. Once removed, I place the circular rubber up to the head of his penis. My eyes widen as I see that the diameter of the ring, that in all of my previous experiences seemed to be equal to the size of the dick, is noticeably smaller than the width of his tip.

I chuckle to myself nervously at the sheer absurdity of his size. “Is there a problem?” he asks from above me.

In my mind, I can already tell that the massiveness of his cock would justify the need for more ample protection. But as my eyes turn to his, I feel the words slip out of my mouth. “No. Of course not.” Perhaps because I refuse to admit that I was wrong. Perhaps because I want to continue.

I hold the condom onto his tip and slowly and carefully begin to roll it over the head. I struggle to hold it in place and apply enough force to get it to actually move down over him, but within a few seconds it begins to move. I work it down gently, eventually covering the tip and moving on to the even thicker shaft.

I feel as if my breath is trapped in my chest as I can hardly wrap my fingers around his impressive girth. I subconsciously take notice that his cock is just about the size of my wrist as I pull the latex down over it. I can feel myself getting wet, just from seeing it and touching it, wondering what it would feel like to be inside me.

I continue unrolling it until it no longer extends, somehow still leaving nearly an inch of his base still uncovered. I remove my hands from his cock and look up to his face. “See? It fits,” I say knowing that it appears to be on the verge of bursting.

He glares at me with a smirk. “You sure about that?” he asks.

“Uh huh,” I reply nervously with a nod.

“You don’t think that there’s any risk of breakage?” he prods.

“N-nope.”

He stares into my eyes intensely. I can feel his energy shift. He doesn’t care about proving his point any longer. He only wants one thing. “Do you care to test that?” I nod my head gently, no longer able to contain my own desire. “Lay back.”

I follow his command and lie down onto his bed. He steps toward me and unfastens the button on my shorts before gripping the waistband and pulling at them. I lift my hips instinctively allowing him to move down the full length of my legs, leaving my lower half completely bare. He tosses my shorts behind him onto a pile of cardboard boxes.

He steps over to his bedside table and opens a drawer. From inside he removes a large clear bottle. He moves himself back before me and pops open the lid before liberally applying the gel onto the already lubricated condom. He coats the entirety of his shaft to prepare himself for entry, before setting the bottle down on the floor at his feet.

He turns his attention to me. “Ready?” he asks. I nod my head timidly as I look at his monstrous cock standing over me, not knowing if he is even going to fit.

He grips his shaft and guides the tip of his dick between my lips. He presses forward firmly but carefully. Despite the combination of his thoroughly lubed cock and my practically dripping pussy, I struggle to accept him as he slides into me. I can feel his girth stretching my insides, forcing me to flinch inadvertently and close my legs to prevent him from pushing further.

He looks into my eyes and speaks. “You’ve got it. Just relax. I’ll go slow.”

I nod my head and close my eyes as I try to loosen myself up. Moments later I feel him start again. I gasp in response to the subtle movement. He gently rocks his hips back and forth, slowly working inside of me allowing my pussy to accommodate his incredible size. I let out long controlled breaths as I try to manage the stretching, tearing feeling occurring within me.

But as time goes on, as his strokes become longer, the discomfort begins to ease. As my vagina becomes more open, more able to handle his girth, I begin to feel something else. A fullness. As his cock slides in and out of me I feel my walls cling to him. I can feel myself melt in pleasure. Suddenly my gasps for managing discomfort shift to moans of pleasure as he buries himself deep within me.

As I become more relaxed, his slow, intentional pumps grow in speed. He smoothly thrusts back and forth. The feeling has become euphoric. With each insertion I can feel my excitement build. My focus drifts, unable to process anything other than the intense sensation being given to me.

I find myself moaning and muttering incoherent half thoughts. “Oh god…yes yes yes…that’s it…oh fuck”

A pressure is forming within me. Each time I feel his dick refill my pussy, I find myself closer to the brink of climax. And it’s clear that he knows. His eyes focus upon my face as he deliberately drives forcefully inside me. Our skin claps as fully sheaths himself within me. I clutch the sheets below me and clench as my body prepares for orgasm when suddenly…

SNAP

Suddenly the sensation inside of me has shifted. I can now feel the warmth of his uncovered skin. He stops his movement, knowing the exact cause of the change. He begins to chuckle and smiles at me. “Told you I needed a bigger size.”

He begins to withdraw himself from me, but still lost to the euphoria of his cock I wrap my legs around him. He looks at me and raises his eyebrows in surprise. “Don’t stop,” I plead. “Please.”

A devilish smile curls up across his face. He powerfully drives his hips forward once again. I moan loudly as he fills me up once more. My head rolls back on to the bed as I relish in the feeling. He places his hands around my hips and presses me onto the mattress to hold me in place as he delivers fast, forceful thrusts.

The urge to cum quickly builds in me once again as he slams into me unrelentingly. My breaths become erratic. I clutch the bed with both hands and throw my head back moaning with increasing volume. My legs squeeze tightly around him as I approach climax.

“OH FUCK!” I exclaim as waves of ecstasy roll through my body.

My legs unclasp from around him and shoot out straight. My hips attempt to jolt up off of the bed, but he uses his strong hands to keep me pinned to keep himself buried deep within me. I can feel my pussy pulse around his thick shaft. My body begins to shake and convulse violently as a warm wave of ecstasy travels through me.

“That’s it. You’ve got it,” he reassures me as I struggle to collect myself.

I inadvertently start to giggle between heavy gasps for air. After another moment I feel him release his grip on my hips. He slowly pulls back, removing himself from me. As the tip of his dick exits my lips, I let out a short breath from the sudden void left within me.

I look between my legs and see his still raging erection. Towards the base he still has the ring of the condom still tightly squeezing his dick with what remains of the condom hanging off below. I laugh as he begins to roll it up towards the tip of his shaft.

He looks at me and smiles. “So do you believe me now?” he asks as he finally pulls the remains of the rubber off of his cock.

I watch him closely and bite my lip before sitting up and replying. “I don’t think I’m really in a position to try and contest that anymore. You are one hundred percent correct.”

“Was that so hard to admit?” he replies cockily. He walks over to where he had tossed my shorts. He picks them up but before he can turn around he double takes back to the box that it had landed on. “Oh shit!”

“What?” I ask curiously.

He leans over and shuffles through the box to get to the bottom. He stands back up and pulls out a small black package with the word ‘TROJAN’ typed across it in shiny gold letters. “They’re here!”

We both begin to laugh as he brings me my clothes. “Well I guess you’ll get to enjoy your date,” I say as I slide my shorts back on.

“I guess so,” he says with a smirk.

“Assuming she can handle it, that is,” I reply as I stand up from his bed.

He chuckles. “That does seem to be an issue at times.”

I step closer to him. “Well that would be rather unfortunate.”

“Yeah. But I could always find someone more suited for it,” he says as he uses a finger to twirl my hair hanging down the side of my face.

“Who knows? They might be closer than you think,” I reply as I run my finger tip down his chest.

“Who knows?” he repeats. He slowly leans toward me, bringing his face close to mine.

I move in as well, but once we are a mere inches from pressing our lips together I whisper. “Good luck on your date.”

I quickly walk out of the room and make my way back down to mine. I close the door behind me and lean against it. I laugh quietly to myself for a moment, still not believing what I had just done. I walk back over to my bed and pick up my book to study once again. But as my eyes scan over the words, I am unable to process anything due to a single overpowering thought of when I will see my roommate again.

The End.

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